Derivatives of beta-picoline and crop protection agents containing them

ABSTRACT

β-picoline derivatives of the formula ##STR1## where A is CR 1  R 2 , R 1  and R 2  independently of each other are hydrogen, alkyl, alkenyl or alkynyl, or R 1  and R 2  together form a methylene chain, 
     B is one of the groups CH 2 , CHOR 3 , CHalR 4 , C═O or C═N-O-R 5 , R 3  being hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, acyl, phenyl, benzyl or benzoyl, where the phenyl ring is substituted or unsubstituted, R 4  being hydrogen, fluorine, chlorine, bromine or iodine, R 5  being hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, phenyl or benzyl, the phenyl ring being substituted or unsubstituted, 
     Ar is a substituted or unsubstituted aryl radical, 
     their N-oxides and plant-tolerated acid addition salts, and fungicides containing these compounds.

The present invention relates to β-picoline derivatives and fungicides containing them.

The compound 1-phenyl-3-(3-pyridinyl)-propan-1-one is disclosed in J. Org. Chem. 43 (1978), 3396 and in Arch. Pharm. 307 (1974), 550, but a fungicidal action is not reported.

We have found that β-picoline derivatives of the formula ##STR2## where A is CR¹ R²,

R¹ and R² independently of one another are each hydrogen, C₁ -C₅ -alkyl, C₂ -C₆ -alkenyl or C₂ -C₆ -alkynylor R¹ and R² together form a methylene chain having from 2 to 6 methylene groups,

B is one of the groups CH₂, CHOR³, CHR⁴, C═O or C═N-O-R⁵,

R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆ -alkenyl, C₂ -C₆ -acyl, phenyl, benzyl or benzoyl, where the phenyl ring may be unsubstituted or substituted by from one to three substituents from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, halogen, cyano and nitro,

R⁴ is hydrogen, fluorine, chlorine, bromine or iodine,

R⁵ is hydrogen, C₁ -C₅ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₇ -cycloalkyl, C₃ -C₆ -alkenyl or aralkyl where the alkyl radical is of 1 to 4 carbon atoms and the aryl radical may be unsubstituted or substituted by from one to three substituents from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, cyano and nitro, and Ar is a mononuclear or dinuclear aryl radical which is unsubstituted or monosubstituted to trisubstituted by halogen, C₁ -C₅ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, phenyl, phenoxy, halophenyl, halophenoxy or benzyloxy,

and their N-oxides and plant-tolerated acid addition salts, except for the compound in which A is CH₂, B is C═O and Ar is phenyl, have a good fungicidal action, which is better than the action of known active ingredients.

R¹ and R² independently of one another are each, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl or propargyl. The radicals CR¹ R² in which R¹ is not hydrogen, in particular the radicals in which R¹ and R² are not hydrogen, are preferred.

R¹ and R² together may furthermore, together with the carbon atom of which they are substituents, form a cycloalkyl ring of 3 to 7 carbon atoms which contains from 2 to 6 methylene groups.

R³ is, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl, propargyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromoethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butylphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl, cyanophenyl, mono-, di- or tribenzyl, 4-tert-butylphenyl, mono-, di- or trimethoxyb-enzyl, trifluoromethylbenzyl, fluorobenzyl, mono-, di- or trichlorobenzyl, mono- or dinitrobenzyl, cyanobenzyl, mono-, di- or trimethylbenzoyl, 4-tert-butylbenzoyl, mono-, di- or trimethoxybenzoyl, trifluoromethylbenzoyl, fluorobenzoyl, mono-, di- or trichlorobenzoyl, mono- or dinitrobenzoyl, cyanobenzoyl, acetyl, propionyl, butyryl, pentanoyl or hexanoyl

R⁵ is, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylally, propargyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromcethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butylphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl, cyanophenyl, mono-, di- or trimethylbenzyl, 4-tert-butylbenzyl, mono-, di- or trimethoxybenzyl, trifluoromethylbenzyl, fluorobenzyl, mono-, di- or trichlorobenzyl, mono- or dinitrobenzyl or cyanobenzyl and Ar is, for example, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 4-isopropyl-phenyl, 4-tert-butylphenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,4,6-trichloropheny-1,2-chloro-4-fluoropheny1,2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-, 3- or 4-methoxyphenyl, 3,4-dimethoxyphenyl, 4-trifluoromethoxyphenyl, 4-tetrafluoroethoxyphenyl- 2-chloro-1,4-phenoxypheny1,4-(4,-chlorophenoxy)-phenyl or 4 -benzyloxyphenyl.

The compounds of the formula I may have two or more centers of asymmetry and can therefore occur in two or more diastereomeric forms, which can be separated by known methods, for example by chromatography or crystallization. The present invention relates both to the pure diastereomers and to mixtures thereof and to their use as fungicides.

The β-picoline derivatives can be prepared by a method in which an aldehyde of the formula II ##STR3## where A has the abovementioned meanings, is reacted with an organometallic compound of the formula III

    Ar-M                                                       (III)

where M is lithium or one of the radicals MgCl, MgBr or MgI and Ar has the abovementioned meanings. It is advantageous initially to take the organometallic compound of the formula III in an inert solvent, preferably an ether, such as diethyl ether or tetrahydrofuran, at from 0 to 80° C., preferably from 0 to 20° C., and to add the aldehyde of the formula II, if necessary dissolved in a diluent.

The organometallic compounds of the formula III are generally known. The aldehydes of the formula II where A is CH₂ or CH(CH₃) are disclosed in J. Org. Chem. 43 (1978), 3396 and 2947. The other aldehydes of the formula II where A has the abovementioned meanings are novel. They can be prepared, for example, by alkylating an aldehyde of the formula IV

    H--A--CHO                                                  (IV)

where A has the abovementioned meanings with the exception of CH₂ and CH(CH₃), with 3-chloromethylpyridine produced in situ, in the presence of a base. 3-Chloromethylpyridine is unstable and tends to form a resin at as low as room temperature (cf. for example CA 47, 8068e). A 3-chloromethylpyridine liberated in situ from the hydrochloride is a suitable reagent for the alkylation of aldehydes.

The direct alpha-alkylation of aldehydes takes place, as a rule, with only poor yields, and the same applies to the enamines derived from the aldehydes (cf. for example G. Opitz et al., Liebigs Ann. Chem. 649 (1961), 36). A simple preparative method is the alphaalkylation of aldehydes under phase transfer catalysis. This process can be carried out as a solid/liquid variant in a two-phase system consisting of solid sodium hydroxide and a lipophilic organic solvent (cf. H. K. Dietl and K. C. Brannock, Tetrahedron Lett. 1273 (1973); E. Buschmann and B. Zeeh, Liebigs Ann. Chem. 1585 (1979)). Particularly advantageous here is a liquid/liquid variant in which the sodium hydroxide solution and an organic, water immiscible solvent and a suitable phase transfer catalyst are initially taken and the aldehyde IV, if necessary dissolved in a diluent, and the 3-chloromethylpyridine hydrochloride, if necessary in the form of an aqueous solution, are metered in. Examples of suitable organic phases are hydrocarbons, such as petroleum ether, cyclohexane, benzene, toluene, xylene or chlorohydrocarbons, such as dichloromethane or 1,2-dichloroethane. For example, crown ethers or quaternary ammonium salts, preferably tetra-n-butylammonium salts, benzyltriethylammonium salts or methyltrioctylammonium salts, can be used as phase transfer catalysts. The reaction is preferably carried out at from 0 to 100° C., in particular from 20 to 80° C. In another process for the preparation of aldehydes of the formula II, an α,β-unsaturated aldehyde of the formula ##STR4## where A is C-(C₁ -C₆ -alkyl), is hydrogenated with hydrogen in the presence of a suitable catalyst. The aldehydes of the formula V are novel. They can be prepared by a method in which the aldehyde ##STR5## is reacted with an aldehyde ##STR6## (similarly to European Patent 298, 380).

The processes for carrying out the oxidation of the alcohols of the general formula I (B═CHOH) are known from the literature (cf. for example Houben-Weyl, Methoden der organischen Chemie, Volume VII/2a, Ketone Part 1, page 699 et seq.). A preferred process is the oxidation with dimethyl sulfoxide in the presence of suitable reagents, for example oxalyl chloride/triethylamine. Suitable diluents are inert organic solvents, for example hydrocarbons, such as petroleum ether, cyclohexane, benzene or chlorohydrocarbons, such as dichloromethane, 1,2-dichloroethane or chloroform, or ethers, eg. diethyl ether, tetrahydrofuran or dioxane. The reaction is carried out at from -80 to 50° C., preferably from -70 to -10° C.

The chlorides of the general formula I where B is H--C--Cl are obtainable from the corresponding hydroxy compounds by methods known from the literature (cf. for example Houben-Weyl, Methoden der organischen Chemie, Volume V/3, Halogenverbindungen).

The reaction of thionyl chloride with the alcohols is a preferably used process. Suitable diluents are inert solvents, for example hydrocarbons, such as petroleum ether, cyclohexane, benzene, toluene or xylene. The reaction is carried out at from 40 to 150° C., preferably 80° C., in the presence or absence of a catalyst. Examples of suitable catalysts are dimethylformamide and tertiary amines, such as triethylamine, N,N-dimethylaniline or piperidine.

The oxime ethers of the general formula I where B is C═R⁵ and R⁵ has the meanings stated in the claim are obtainable by conventional processes (cf. Houben-Weyl, Methoden der organischen Chemie, X, 4/55).

A preferably used process is the reaction of the ketones of the general formula I where B is C═O and a hydroxylamine in a suitable diluent and suitable reagents. Suitable diluents are inert organic solvents, for example hydrocarbons, such as petroleum ether, cyclohexane or benzene, or chlorohydrocarbons, such as dichloromethane, 1,2-dichloroethane or chloroform, ethers, eg. diethyl ether, tetrahydrofuran or dioxane, nitriles, such as acetonitrile or propionitrile, and alcohols, such as methanol, ethanol or n-butanol.

Suitable reaction assistants are all conventional inorganic and organic bases, for example alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide, alkali metal alcoholates, such as sodium methylate, sodium ethylate or potassium tert-butylate, alkali metal carbonates, such as sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, and tertiary amines, such as triethylamine, N,N-dimethylaniline or piperidine.

The reaction is carried out at from 20 to 150° C., preferably from 50 to 130° C.

The N-oxides can be prepared by oxidizing the β-picoline derivatives of the formula I.

Plant-tolerated acid addition salts are salts of the β-picoline derivatives of the formula I with inorganic or organic acids, for example sulfuric acid, phosphoric acid, acetic acid, propionic acid, oxalic acid, phenylsulfonic acid or dodecylbenzenesulfonic acid.

The methods and Examples which follow illustrate the preparation of the intermediates and of the novel compounds.

Method 1 2-(Pyrid-3-ylmethyl)-hexanol

A mixture of 21 g (0.11 mol) of 2-butyl-3-pyridylpropenal, 120 ml of methanol, 10 g of N-methylmorpholine and 6 g of a hydrogenation catalyst (10% of Pd and 5% of Pr₂ O₃ on Al₂ O₃) is hydrogenated at 75° C. and 75 bar hydrogen pressure in a 0.3 1 stirred autoclave until the pressure remains constant. The solution is filtered under suction over silica gel, the filtrate is evaporated down under reduced pressure and the residue is purified by distillation.

Yield: 24.1 g (56.8%) ##STR7##

Method 2 2-(Pyrid-3-ylmethyl)-hexanal

23 g (0.132 mol) of dimethy sulfoxide in 120 ml of CH₂ Cl₂ are added dropwise in the course of one hour to 17 g (0.132 mol) of oxalyl chloride in 280 ml of CH₂ Cl₂ at -60° C. Thereafter, 23 g (0.12 mol) of 2-(pyrid-3-yl-methyl)-hexanol in 240 ml of CH₂ Cl₂ are slowly added, followed by 62 g of triethylamine after 30 minutes.

The mixture is allowed to reach room temperature (RT, 20° C.) slowly and 350 ml of H₂ O are added. The aqueous phase is extracted with 3×300 ml of CH₂ Cl₂ and the combined methylene chloride phases are washed with NaHCO₃ solution. Drying is carried out over Na₂ SO₄, the solvent is evaporated off and the residue is then subjected to distillation. 8.2 g (36%) of the title compound (118-120° C., 0.7 mmHg) are obtained. ##STR8##

Method 3 2-Ethyl-2-(pyrid-3-ylmethyl)-butanal

A solution of 98.4 g (0.6 mol) of β-picoline chloride hydrochloride and 66 g (0.66 mol) of 2-ethylbutanal in 600 ml of toluene is added dropwise in the course of 3 hours to a mixture of 450 ml of toluene, 600 ml of 30% strength by weight NaOH (4.5 mol) and 7.5 g of tetrabutylammonium iodide at 80° C.

Stirring is then carried out for a further 3 hours at this temperature, the mixture is cooled and 1,000 ml of toluene are then added. The organic phase is separated off, washed three times with water, dried and evaporated down.

Distillation (128-132° C./2 mmHg) gives 56 g (49%) of the title compound.

EXAMPLE 1 2-Ethyl-1-(4-fluorophenyl)-2-(pyrid-3-ylmethyl)-butan-1-ol

20.4 g (0.116 mol) of 4-fluorobromobenzene in 250 ml of tetrahydrofuran are added dropwise to 2.8 g of magnesium turnings (0.166 mol) and stirring is carried out for half an hour at RT. 11 g (0.058 mol) of 2-ethyl-2-(pyrid-3-ylmethyl)-butanal in 100 ml of tetrahydrofuran are then slowly added dropwise. After 2 hours, the mixture is poured onto ice water and brought to pH 8 with saturated NH₄ Cl solution. It is extracted with ether, the organic phase is washed with water and dried over Na₂ SO₄ and the solvent is then evaporated off. 8 g (48%) of the title compound are obtained as a viscous oil (compound No. 70 in the Table).

EXAMPLE 2 2Ethyl-1-(4-fluorophenyl)-2-(pyrid-30-0ylmethyl)-butan-1-one

22.5 g (0.288 mol) of dimethyl sulfoxide in 50 ml of methylene chloride are added dropwise to 18.6 g (0.144 mol) of oxalyl chloride in 200 ml of CH₂ Cl₂ at -60° C. The reaction is allowed to continue for 5 minutes at -60° C.

33 g (0.115 mol) of 2-ethyl-1-(4-fluorophenyl)-2-(pyrid-3-ylmethyl)-butanol in 100 ml of CH₂ Cl₂ are then slowly added and, after 15 minutes, 58.2 g (0.576 mol) of triethylamine are introduced. The mixture is allowed to reach RT slowly, 350 ml of water are added, the aqueous phase is extracted with 3×200 ml of CH₂ Cl₂ and the combined organic phases are dried over Na₂ SO₄. After the solvent has been evaporated off, the title compound is obtained in a yield of 49% (compound No. 331).

EXAMPLE 3 1-Chloro-2-ethyl-1-phenyl-2-(pyrid-3-ylmethyl)-butane

13.3 g (0.11 mol) of SOCl₂ are added dropwise, at 80° C., to 5 g (0.018 mol) of 2-ethyl-1-phenyl-2-(pyrid-3-ylmethyl)-butanol in 100 ml of toluene and a catalytic amount (0.1 g) of dimethylformamide, and the mixture is left for 5 hours at this temperature. The mixture is cooled, poured onto ice water and then rendered alkaline with 30% strength NaOH solution. The aqueous phase is extracted with three times 50 ml of tert-butyl methyl ether and the combined organic phases are dried over MgSO₄. After the solvent has been evaporated off, the residue is chromatographed over silica gel (1 : 1 toluene/ethyl acetate). 2.07 g (yield 40%) of the title compound are obtained as a viscous yellow oil (compound No. 581).

The compounds listed in the Table below can be prepared in a similar manner.

                                      TABLE                                        __________________________________________________________________________     No.                                                                               A         B       Ar                Phys. data IR, cm.sup.-1                __________________________________________________________________________      1 C(CH.sub.3).sub.2                                                                        CHOH    Phenyl            oil 2963, 1449, 1424, 1361, 1059,                                              1045                                     2 C(CH.sub.3).sub.2                                                                        CHOH    2-Methylphenyl    107-110° C.                       3 C(CH.sub.3).sub.2                                                                        CHOH    4-Methylphenyl    oil 3146, 1474, 1426, 1069, 1045,                                              824                                      4 C(CH.sub.3).sub.2                                                                        CHOH    2,4-Dimethylphenyl                                         5 C(CH.sub.3).sub.2                                                                        CHOH    2,6-Diemthylphenyl                                         6 C(CH.sub.3).sub.2                                                                        CHOH    2,4,6-Trimethylphenyl                                                                            155-157° C.                       7 C(CH.sub.3).sub.2                                                                        CHOH    4-tert. Butylphenyl                                                                              144-146° C.                       8 C(CH.sub.3).sub.2                                                                        CHOH    1-Naphtyl                                                  9 C(CH.sub.3).sub.2                                                                        CHOH    2-Napthyl                                                  10                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Biphenyl                                                 11                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2-Fluorophenyl                                             12                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Fluorophenyl    oil 3200, 2966, 2871, 1602, 1508,                                              1424                                     13                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2,4-Difluorophenyl                                         14                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2-Chlorophenyl                                             15                                                                               C(CH.sub.3).sub.2                                                                        CHOH    3-Chlorophenyl                                             16                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Chlorophenyl    oil 3200, 2966, 2934, 2870, 1486,                                              1424                                     17                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2,4-Dichlorophenyl                                                                               oil 3300, 2967, 1587, 1467, 717          18                                                                               C(CH.sub.3).sub.2                                                                        CHOH    3,4-Dichlorophenyl                                         19                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2-Chloro-4-fluorophenyl                                    20                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2-Trifluoromethylphenyl                                    21                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Trifluoromethylphenyl                                    22                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Methoxyphenyl   oil 3250, 2961, 1610, 1511, 1247         23                                                                               C(CH.sub.3).sub.2                                                                        CHOH    3,4-Dimethoxyphenyl                                        24                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Tetrafluoroethoxyphenyl                                  25                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Trifluoromethoxyphenyl                                   26                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                        27                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Phenoxyphenyl                                            28                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-(4'-Chlorophenoxy)phenyl                                 29                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Benzyloxyphenyl                                          30                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    Phenyl            oil 3200, 2964, 2936, 2877, 1463,                                              1452                                     31                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Methylphenyl                                             32                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Methylphenyl    oil 3200, 2964, 2936, 2877, 1478,                                              1463, 1424                               33                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2,4-Dimethylphenyl                                         34                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2,6-Dimethylphenyl                                         35                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2,4,6-Trimethylphenyl                                      36                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-tert. Butylphenyl                                        37                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    1-Naphthyl                                                 38                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Naphthyl                                                 39                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Biphenyl                                                 40                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Fluorophenyl                                             41                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Fluorophenyl    oil 3200, 2965, 2937, 1602, 1508,                                              1424                                     42                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2,4-Difluorophenyl                                         43                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Chlorophenyl                                             44                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    3-Chlorophenyl                                             45                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Chlorophenyl    oil 3190, 2965, 2936, 2877, 1486,                                              1464                                     46                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2,4-Dichlorophenyl                                         47                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    3,4-Dichlorophenyl                                         48                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Chloro-4-fluorophenyl                                    49                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Trifluoromethylphenyl                                    50                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Trifluoromethylphenyl                                    51                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Methoxyphenyl                                            52                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    3,4-Dimethoxyphenyl                                        53                                                                               C(CH.sub.3)(CH.sub.2 CH.sub. 3)                                                          CHOH    4-Tetrafluoroethoxyphenyl                                  54                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Trifluoromethoxyphenyl                                   55                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                        56                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Phenoxyphenyl                                            57                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-(4'-Chlorophenoxy)phenyl                                 58                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHOH    4-Benzyloxyphenyl                                          59                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    Phenyl            oil 3203, 2963, 2935, 2879, 1452,                                              1424                                     60                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Methylphenyl    oil 3320, 2963, 1425, 1030, 758,                                               718                                      61                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Methylphenyl    oil 2965, 2936, 2879, 1478, 1455,                                              1424                                     62                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2,4-Dimethylphenyl                                         63                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2,6-Dimethylphenyl                                         64                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2,4,6-Trimethylphenyl                                                                            161-164° C.                       65                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-tert. Butylphenyl                                        66                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    1-Naphthyl                                                 67                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Naphthyl                                                 68                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Biphenyl                                                 69                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Fluorophenyl                                             70                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Fluorophenyl    oil 3200, 2966, 2937, 2879, 1602,                                              1507                                     71                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2,4-Difluorophenyl                                         72                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Chlorophenyl                                             73                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    3-Chlorophenyl                                             74                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Chlorophenyl    oil 3200, 2966, 2937, 2878, 1487,                                              1424                                     75                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2,4-Dichlorophenyl                                                                               mp. 142-144° C.                   76                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    3,4-Dichlorophenyl                                         77                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Chloro-4-fluorophenyl                                    78                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Trifluoromethylphenyl                                    79                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Trifluoromethylphenyl                                    80                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Methoxyphenyl   oil 3200, 2963, 1510, 1246, 1031,                                              717                                      81                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    3,4-Dimethoxyphenyl                                        82                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Tetrafluoroethoxyphenyl                                  83                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Trifluoromethoxyphenyl                                   84                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                        85                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Phenoxyphenyl                                            86                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-(4'-Chlorophenoxy)phenyl                                 87                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHOH    4-Benzyloxyphenyl                                          88                                                                               Cyclopropylene                                                                           CHOH    Phenyl            oil 3231, 3027, 1424, 1028, 715,                                               702                                      89                                                                               Cyclopropylene                                                                           CHOH    2-Methylphenyl                                             90                                                                               Cyclopropylene                                                                           CHOH    4-Methylphenyl    oil 3238, 2921, 1424, 1044, 820,                                               716                                      91                                                                               Cyclopropylene                                                                           CHOH    2,4-Dimethylphenyl                                         92                                                                               Cyclopropylene                                                                           CHOH    2,6-Dimethylphenyl                                         93                                                                               Cyclopropylene                                                                           CHOH    2,4,6-Trimethylphenyl                                      94                                                                               Cyclopropylene                                                                           CHOH    4-tert. Butylphenyl                                        95                                                                               Cyclopropylene                                                                           CHOH    1-Naphthyl                                                 96                                                                               Cyclopropylene                                                                           CHOH    2-Naphthyl                                                 97                                                                               Cyclopropylene                                                                           CHOH    4-Biphenyl                                                 98                                                                               Cyclopropylene                                                                           CHOH    4-Fluorophenyl                                             99                                                                               Cyclopropylene                                                                           CHOH    4-Fluorophenyl    oil 3200, 2940, 1508, 1221, 838         100                                                                               Cyclopropylene                                                                           CHOH    2,4-Difluorophenyl                                        101                                                                               Cyclopropylene                                                                           CHOH    2-Chlorophenyl                                            102                                                                               Cyclopropylene                                                                           CHOH    3-Chlorophenyl                                            103                                                                               Cyclopropylene                                                                           CHOH    4-Chlorophenyl    oil 3200, 2924, 1425, 1014, 717         104                                                                               Cyclopropylene                                                                           CHOH    2,4-Dichlorophenyl                                        105                                                                               Cyclopropylene                                                                           CHOH    3,4-Dichlorophenyl                                        106                                                                               Cyclopropylene                                                                           CHOH    2-Chloro-4-fluorophenyl                                   107                                                                               Cyclopropylene                                                                           CHOH    2-Trifluoromethylphenyl                                   108                                                                               Cyclopropylene                                                                           CHOH    4-Trifluoromethylphenyl                                   109                                                                               Cyclopropylene                                                                           CHOH    4-Methoxyphenyl                                           110                                                                               Cyclopropylene                                                                           CHOH    3,4-Dimethoxyphenyl                                       111                                                                               Cyclopropylene                                                                           CHOH    4-Tetrafluoroethoxyphenyl                                 112                                                                               Cyclopropylene                                                                           CHOH    4-Trifluoromethoxyphenyl                                  113                                                                               Cyclopropylene                                                                           CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                       114                                                                               Cyclopropylene                                                                           CHOH    4-Phenoxyphenyl                                           115                                                                               Cyclopropylene                                                                           CHOH    4-(4'-Chlorophenoxy)phenyl                                116                                                                               Cyclopropylene                                                                           CHOH    4-Benzyloxyphenyl                                         117                                                                               Cyclopentylene                                                                           CHOH    Phenyl            oil 3211, 2953, 2869, 1478, 1451,                                              1424                                    118                                                                               Cyclopentylene                                                                           CHOH    2-Methylphenyl    oil 3225, 2954, 1442, 1031, 740,                                               719                                     119                                                                               Cyclopentylene                                                                           CHOH    4-Methylphenyl    oil 3225, 2952, 2869, 1478, 1451,                                              1424                                    120                                                                               Cyclopentylene                                                                           CHOH    2,4-Dimethylphenyl                                        121                                                                               Cyclopentylene                                                                           CHOH    2,6-Dimethylphenyl                                        122                                                                               Cyclopentylene                                                                           CHOH    2,4,6-Trimethylphenyl                                                                            141-142° C.                      123                                                                               Cyclopentylene                                                                           CHOH    4-tert. Butylphenyl                                       124                                                                               Cyclopentylene                                                                           CHOH    1-Naphthyl                                                125                                                                               cyclopentylene                                                                           CHOH    2-Naphthyl                                                126                                                                               Cyclopentylene                                                                           CHOH    4-Biphenyl                                                127                                                                               Cyclopentylene                                                                           CHOH    2-Fluorophenyl                                            128                                                                               Cyclopentylene                                                                           CHOH    4-Fluorophenyl    oil 3200, 2954, 2871, 1603, 1507,                                              1425                                    129                                                                               Cyclopentylene                                                                           CHOH    2,4-Difluorophenyl                                        130                                                                               Cyclopentylene                                                                           CHOH    2-Chlorophenyl                                            131                                                                               Cyclopentylene                                                                           CHOH    3-Chlorophenyl                                            132                                                                               Cyclopentylene                                                                           CHOH    4-Chlorophenyl    oil 2954, 2870, 1484, 1090, 1046,                                              1030                                    133                                                                               Cyclopentylene                                                                           CHOH    2,4-Dichlorophenyl                                                                               mp. 150-151° C. 3270, 2952,                                             2872, 2706, 2625, 1541                  134                                                                               Cyclopentylene                                                                           CHOH    3,4-Dichlorophenyl                                        135                                                                               Cyclopentylene                                                                           CHOH    2-Chloro-4-fluorophenyl                                   136                                                                               Cyclopentylene                                                                           CHOH    2-Trifluoromethylphenyl                                   137                                                                               Cyclopentylene                                                                           CHOH    4-Trifluoromethylphenyl                                   138                                                                               Cyclopentylene                                                                           CHOH    4-Methoxyphenyl   91-93° C.                        139                                                                               Cyclopentylene                                                                           CHOH    3,4-Dimethoxyphenyl                                       140                                                                               Cyclopentylene                                                                           CHOH    4-Tetrafluoroethoxyphenyl                                 141                                                                               Cyclopentylene                                                                           CHOH    4-Trifluoromethoxyphenyl                                  142                                                                               Cyclopentylene                                                                           CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                       143                                                                               Cyclopentylene                                                                           CHOH    4-Phenoxyphenyl                                           144                                                                               Cyclopentylene                                                                           CHOH    4-(4'-Chlorophenoxy)phenyl                                145                                                                               Cyclopentylene                                                                           CHOH    4-Benzyloxyphenyl                                         146                                                                               Cyclohexylene                                                                            CHOH    Phenyl            oil 2933, 2860, 1454, 1424, 1067,                                              1042                                    147                                                                               Cyclohexylene                                                                            CHOH    2-Methylphenyl    oil 3200, 2934, 1458, 1069, 737,                                               719                                     148                                                                               Cyclohexylene                                                                            CHOH    4-Methylphenyl    oil 2933, 2860, 1456, 1423, 1069,                                              1042                                    149                                                                               Cyclohexylene                                                                            CHOH    2,4-Dimethylphenyl                                        150                                                                               Cyclohexylene                                                                            CHOH    2,6-Dimethylphenyl                                        151                                                                               Cyclohexylene                                                                            CHOH    2,4,6-Trimethylphenyl                                                                            164° C.                          152                                                                               Cyclohexylene                                                                            CHOH    4-tert. Butylphenyl                                                                              167-169° C.                      153                                                                               Cyclohexylene                                                                            CHOH    1-Naphthyl                                                154                                                                               Cyclohexylene                                                                            CHOH    2-Naphthyl                                                155                                                                               Cyclohexylene                                                                            CHOH    4-Biphenyl                                                156                                                                               Cyclohexylene                                                                            CHOH    2-Fluorophenyl                                            157                                                                               Cyclohexylene                                                                            CHOH    4-Fluorophenyl    mp. 133-135° C.                                                         3264, 2928, 2862, 1507, 1453,                                                  1428, 1222                              158                                                                               Cyclohexylene                                                                            CHOH    2,4-Difluorophenyl                                        159                                                                               Cyclohexylene                                                                            CHOH    2-Chlorophenyl                                            160                                                                               Cyclohexylene                                                                            CHOH    3-Chlorophenyl                                            161                                                                               Cyclohexylene                                                                            CHOH    4-Chlorophenyl    oil 3152, 2931, 1480, 1427, 1076,                                              717                                     162                                                                               Cyclohexylene                                                                            CHOH    2,4-Dichlorophenyl                                                                               140-141° C.                      163                                                                               Cyclohexylene                                                                            CHOH    3,4-Dichlorophenyl                                        164                                                                               Cyclohexylene                                                                            CHOH    2-Chloro-4-fluorophenyl                                   165                                                                               Cyclohexylene                                                                            CHOH    2-Trifluoromethylphenyl                                   166                                                                               Cyclohexylene                                                                            CHOH    4-Trifluoromethylphenyl                                   167                                                                               Cyclohexylene                                                                            CHOH    4-Methoxyphenyl   126-129° C.                      168                                                                               Cyclohexylene                                                                            CHOH    3,4-Dimethoxyphenyl                                       169                                                                               Cyclohexylene                                                                            CHOH    4-Tetrafluoroethoxyphenyl                                 170                                                                               Cyclohexylene                                                                            CHOH    4-Trifluoromethoxyphenyl                                  171                                                                               Cyclohexylene                                                                            CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                       172                                                                               Cyclohexylene                                                                            CHOH    4-Phenoxyphenyl                                           173                                                                               Cyclohexylene                                                                            CHOH    4-(4'-Chlorophenoxy)phenyl                                174                                                                               Cyclohexylene                                                                            CHOH    4-Benzyloxyphenyl                                         175                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    Phenyl            oil 2958, 2933, 2871, 1452, 1424,                                              1068                                    176                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Methylphenyl                                            177                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Methylphenyl    oil 2958, 2933, 2870, 1467, 1456,                                              1424                                    178                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2,4-Dimethylphenyl                                        179                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2,6-Dimethylphenyl                                        180                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2,4,6-Trimethylphenyl                                     181                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-tert. Butylphenyl                                       182                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    1-Naphthyl                                                183                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Naphthyl                                                184                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Biphenyl                                                185                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Fluorophenyl                                            186                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Fluorophenyl    oil 2959, 2934, 2871, 1508, 1425,                                              1223                                    187                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2,4-Difluorophenyl                                        188                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Chlorophenyl                                            189                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    3-Chlorophenyl                                            190                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Chlorophenyl    oil 2958, 2933, 2871, 1486, 1424,                                              1090                                    191                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2,4-Dichlorophenyl                                        192                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    3,4-Dichlorophenyl                                        193                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Chloro-4-fluorophenyl                                   194                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Trifluoromethylphenyl                                   195                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Trifluoromethylphenyl                                   196                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Methoxyphenyl                                           197                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    3,4-Dimethoxyphenyl                                       198                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Tetrafluoroethoxyphenyl                                 199                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Trifluoromethoxyphenyl                                  200                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                       201                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-Phenoxyphenyl                                           202                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHOH    4-(4'-Chlorophenoxy)phenyl                                203                                                                               C(CH.sub.3)(C.sub. 3 H.sub.7)                                                            CHOH    4-Benzyloxyphenyl                                         204                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    Phenyl            oil 3196, 2956, 2934, 2869, 1452,                                              1424                                    205                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Methylphenyl                                            206                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Methylphenyl    oil 3200, 2956, 2933, 2870, 1478,                                              1457                                    207                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2,4-Dimethylphenyl                                        208                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2,6-Dimethylphenyl                                        209                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2,4,6-Trimethylphenyl                                     210                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-tert. Butylphenyl                                       211                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    1-Naphthyl                                                212                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Naphthyl                                                213                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Biphenyl                                                214                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Fluorophenyl                                            215                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Fluorophenyl    oil 3198, 2957, 2935, 2870, 1603,                                              1507                                    216                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2,4-Difluorophenyl                                        217                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Chlorophenyl                                            218                                                                               C(C.sub.2 H.sub. 5)(n-C.sub.4 H.sub.9)                                                   CHOH    3-Chlorophenyl                                            219                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Chlorophenyl    oil 2957, 2934, 2870, 1487, 1458,                                              1424                                    220                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2,4-Dichlorophenyl                                        221                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    3,4-Dichlorophenyl                                        222                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Chloro-4-fluorophenyl                                   223                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Trifluoromethylphenyl                                   224                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Trifluoromethylphenyl                                   225                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Methoxyphenyl                                           226                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    3,4-Dimethoxyphenyl                                       227                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Tetrafluoroethoxyphenyl                                 228                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Trifluoromethoxyphenyl                                  229                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    2-Chloro-4-(4'-chlorophenoxy)-phenyl                      230                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Phenoxyphenyl                                           231                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-(4'-Chlorophenoxy)phenyl                                232                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHOH    4-Benzyloxyphenyl                                         233                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    Phenyl                                                    234                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2-Methylphenyl                                            235                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Methylphenyl                                            236                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2,4-Dimethylphenyl                                        237                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2,6-Dimethylphenyl                                        238                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2,4,6-Trimethylphenyl                                     239                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-tert. Butylphenyl                                       240                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    1-Naphthyl                                                241                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2-Naphthyl                                                242                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Biphenyl                                                243                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2-Fluorophenyl                                            244                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Fluorophenyl    oil 2.90, 2.75 (dd, 2H, --CH.sub.2                                             -Py)                                    245                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2,4-Difluorophenyl                                        246                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2-Chlorophenyl                                            247                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    3-Chlorophenyl                                            248                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Chlorophenyl                                            249                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2,4-Dichlorophenyl                                        250                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    3,4-Dichlorophenyl                                        251                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2-Chloro-4-fluorophenyl                                   252                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    2-Trifluoromethylphenyl                                   253                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Trifluoromethylphenyl                                   254                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Methoxyphenyl                                           255                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    3,4-Dimethoxyphenyl                                       256                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Tetrafluoroethoxyphenyl                                 257                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Trifluoromethoxyphenyl                                  258                                                                               CH(tert.C.sub.4 H.sub.9 )                                                                CHOH    2-Chloro-4-(4'-chlorophenoxy)phenyl                       259                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Phenoxyphenyl                                           260                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-(4'-Chlorophenoxy)phenyl                                261                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHOH    4-Benzyloxyphenyl                                         262                                                                               C(CH.sub.3).sub.2                                                                        C═O Phenyl                                                    263                                                                               C(CH.sub.3).sub.2                                                                        C═O 2-Methylphenyl                                            264                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Methylphenyl    oil 3.05 (s, 2H, --CH.sub.2 -Py)        265                                                                               C(CH.sub.3).sub.2                                                                        C═O 2,4-Dimethylphenyl                                        266                                                                               C(CH.sub.3).sub.2                                                                        C═O 2,6-Dimethylphenyl                                        267                                                                               C(CH.sub.3).sub.2                                                                        C═O 2,4,6-Trimethylphenyl                                     268                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-tert. Butylphenyl                                       269                                                                               C(CH.sub.3).sub.2                                                                        C═O 1-Naphthyl                                                270                                                                               C(CH.sub.3).sub.2                                                                        C═O 2-Naphthyl                                                271                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Biphenyl                                                272                                                                               C(CH.sub.3).sub.2                                                                        C═O 2-Fluorophenyl                                            273                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Fluorophenyl    oil 2932, 1670, 1588, 1479, 1453,                                              1423                                    274                                                                               C(CH.sub.3).sub.2                                                                        C═O 2,4-Difluorophenyl                                        275                                                                               C(CH.sub.3).sub.2                                                                        C═O 2-Chlorophenyl                                            276                                                                               C(CH.sub.3).sub.2                                                                        C═O 3-Chlorophenyl                                            277                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Chlorophenyl    oil 3.05 (s, 2H, --CH.sub.2 -Py)        278                                                                               C(CH.sub.3).sub.2                                                                        C═O 2,4-Dichlorophenyl                                        279                                                                               C(CH.sub.3).sub.2                                                                        C═O 3,4-Dichlorophenyl                                        280                                                                               C(CH.sub.3 ).sub.2                                                                       C═O 2-Chloro-4-fluorophenyl                                   281                                                                               C(CH.sub.3).sub.2                                                                        C═O 2-Trifluoromethylphenyl                                   282                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Trifluoromethylphenyl                                   283                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Methoxyphenyl                                           284                                                                               C(CH.sub.3).sub.2                                                                        C═O 3,4-Dimethoxyphenyl                                       285                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Tetrafluoroethoxyphenyl                                 286                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Trifluoromethoxyphenyl                                  287                                                                               C(CH.sub.3).sub.2                                                                        C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       288                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Phenoxyphenyl                                           289                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-(4'-Chlorophenoxy)phenyl                                290                                                                               C(CH.sub.3).sub.2                                                                        C═O 4-Benzyloxyphenyl                                         291                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O Phenyl                                                    292                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Methylphenyl                                            293                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Methylphenyl                                            294                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2,4-Dimethylphenyl                                        295                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2,6-Dimethylphenyl                                        296                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2,4,6-Trimethylphenyl                                     297                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-tert. Butylphenyl                                       298                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 1-Naphthyl                                                299                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Naphthyl                                                300                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Biphenyl                                                301                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Fluorophenyl                                            302                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Fluorophenyl                                            303                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2,4-Difluorophenyl                                        304                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Chlorophenyl                                            305                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 3-Chlorophenyl                                            306                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Chlorophenyl                                            307                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2,4-Dichlorophenyl                                        308                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 3,4-Dichlorophenyl                                        309                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Chloro-4-fluorophenyl                                   310                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Trifluoromethylphenyl                                   311                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Trifluoromethylphenyl                                   312                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Methoxyphenyl                                           313                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 3,4-Dimethoxyphenyl                                       314                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Tetrafluoroethoxyphenyl                                 315                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Trifluoromethoxyphenyl                                  316                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       317                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Phenoxyphenyl                                           318                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-(4'-Chlorophenoxy)phenyl                                319                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           C═O 4-Benzyloxyphenyl                                         320                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O Phenyl                                                    321                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═ O                                                                               2-Methylphenyl                                            322                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Methylphenyl                                            323                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2,4-Dimethylphenyl                                        324                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2,6-Dimethylphenyl                                        325                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2,4,6-Trimethylphenyl                                     326                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-tert. Butylphenyl                                       327                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 1-Naphthyl                                                328                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2-Naphthyl                                                329                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Biphenyl                                                330                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2-Fluorophenyl                                            331                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Fluorophenyl    oil 3.08 (s, 2H, --CH.sub.2 -Py)        332                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2,4-Difluorophenyl                                        333                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2-Chlorophenyl                                            334                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 3-Chlorophenyl                                            335                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Chlorophenyl                                            336                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2,4-Dichlorophenyl                                        337                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 3,4-Dichlorophenyl                                        338                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2-Chloro-4-fluorophenyl                                   339                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2-Trifluoromethylphenyl                                   340                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Trifluoromethylphenyl                                   341                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Methoxyphenyl                                           342                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 3,4-Dimethoxyphenyl                                       343                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Tetrafluoroethoxyphenyl                                 344                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Trifluoromethoxyphenyl                                  345                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       346                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Phenoxyphenyl                                           347                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-(4'-Chlorophenoxy)phenyl                                348                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               C═O 4-Benzyloxyphenyl                                         349                                                                               Cyclopropylene                                                                           C═O Phenyl                                                    350                                                                               Cyclopropylene                                                                           C═O 2-Methylphenyl                                            351                                                                               Cyclopropylene                                                                           C═O 4-Methylphenyl    oil 1671, 1808, 1423, 1177, 831,                                               715                                     352                                                                               Cyclopropylene                                                                           C═O 2,4-Dimethylphenyl                                        353                                                                               Cyclopropylene                                                                           C═O 2,6-Dimethylphenyl                                        354                                                                               Cyclopropylene                                                                           C═O 2,4,6-Trimethylphenyl                                     355                                                                               Cyclopropylene                                                                           C═O 4-tert. Butylphenyl                                       356                                                                               Cyclopropylene                                                                           C═O 1-Naphthyl                                                357                                                                               Cyclopropylene                                                                           C═O 2-Naphthyl                                                358                                                                               Cyclopropylene                                                                           C═O 4-Biphenyl                                                359                                                                               Cyclopropylene                                                                           C═O 2-Fluorophenyl                                            360                                                                               Cyclopropylene                                                                           C═O 4-Fluorophenyl    oil 1676, 1600, 1505, 1229, 848,                                               715                                     361                                                                               Cyclopropylene                                                                           C═O 2,4-Difluorophenyl                                        362                                                                               Cyclopropylene                                                                           C═O 2-Chlorophenyl                                            363                                                                               Cyclopropylene                                                                           C═O 3-Chlorophenyl                                            364                                                                               Cyclopropylene                                                                           C═O 4-Chlorophenyl    oil 1675, 1589, 1424, 1051, 841,                                               715                                     365                                                                               Cyclopropylene                                                                           C═O 2,4-Dichlorophenyl                                        366                                                                               Cyclopropylene                                                                           C═O 3,4-Dichlorophenyl                                        367                                                                               Cyclopropylene                                                                           C═O 2-Chloro-4-fluorophenyl                                   368                                                                               Cyclopropylene                                                                           C═O 2-Trifluoromethylphenyl                                   369                                                                               Cyclopropylene                                                                           C═O 4-Trifluoromethylphenyl                                   370                                                                               Cyclopropylene                                                                           C═O 4-Methoxyphenyl                                           371                                                                               Cyclopropylene                                                                           C═O 3,4-Dimethyloxyphenyl                                     372                                                                               Cyclopropylene                                                                           C═O 4-Tetrafluoroethoxyphenyl                                 373                                                                               Cyclopropylene                                                                           C═O 4-Trifluoromethoxyphenyl                                  374                                                                               Cyclopropylene                                                                           C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       375                                                                               Cyclopropylene                                                                           C═O 4-Phenoxyphenyl                                           376                                                                               Cyclopropylene                                                                           C═O 4-(4'-Chlorophenoxy)phenyl                                377                                                                               Cyclopropylene                                                                           C═O 4-Benzyloxyphenyl                                         378                                                                               Cyclopentylene                                                                           C═O Phenyl                                                    379                                                                               Cyclopentylene                                                                           C═O 2-Methylphenyl                                            380                                                                               Cyclopentylene                                                                           C═O 4-Methylphenyl                                            381                                                                               Cyclopentylene                                                                           C═O 2,4-Dimethylphenyl                                        382                                                                               Cyclopentylene                                                                           C═O 2,6-Dimethylphenyl                                        383                                                                               Cyclopentylene                                                                           C═O 2,4,6-Trimethylphenyl                                     384                                                                               Cyclopentylene                                                                           C═O 4-tert. Butylphenyl                                       385                                                                               Cyclopentylene                                                                           C═O 1-Naphthyl                                                386                                                                               Cyclopentylene                                                                           C═O 2-Naphthyl                                                387                                                                               Cyclopentylene                                                                           C═O 4-Biphenyl                                                388                                                                               Cyclopentylene                                                                           C═O 2-Fluorophenyl                                            389                                                                               Cyclopentylene                                                                           C═O 4-Fluorophenyl    oil 3.15 (s, 2H, --CH.sub.2 -Py)        390                                                                               Cyclopentylene                                                                           C═O 2,4-Difluorophenyl                                        391                                                                               Cyclopentylene                                                                           C═O 2-Chlorophenyl                                            392                                                                               Cyclopentylene                                                                           C═O 3-Chlorophenyl                                            393                                                                               Cyclopentylene                                                                           C═O 4-Chlorophenyl    oil 3.15 (s, 2H, --CH.sub.2 -Py)        394                                                                               Cyclopentylene                                                                           C═O 2,4-Dichlorophenyl                                                                               oil 1691, 1583, 1423, 1105, 825,                                               717                                     395                                                                               Cyclopentylene                                                                           C═O 3,4-Dichlorophenyl                                        396                                                                               Cyclopentylene                                                                           C═O 2-Chloro-4-fluorophenyl                                   397                                                                               Cyclopentylene                                                                           C═O 2-Trifluoromethylphenyl                                   398                                                                               Cyclopentylene                                                                           C═O 4-Trifluoromethylphenyl                                   399                                                                               Cyclopentylene                                                                           C═O 4-Methoxyphenyl                                           400                                                                               Cyclopentylene                                                                           C═O 3,4-Dimethoxyphenyl                                       401                                                                               Cyclopentylene                                                                           C═O 4-Tetrafluoroethoxyphenyl                                 402                                                                               Cyclopentylene                                                                           C═O 4-Trifluoromethoxyphenyl                                  403                                                                               Cyclopentylene                                                                           C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       404                                                                               Cyclopentylene                                                                           C═O 4-Phenoxyphenyl                                           405                                                                               Cyclopentylene                                                                           C═O 4-(4'-Chlorophenoxy)phenyl                                406                                                                               Cyclopentylene                                                                           C═O 4-Benzyloxyphenyl                                         407                                                                               Cyclohexylene                                                                            C═O Phenyl                                                    408                                                                               Cyclohexylene                                                                            C═O 2-Methylphenyl                                            409                                                                               Cyclohexylene                                                                            C═O 4-Methylphenyl                                            410                                                                               Cyclohexylene                                                                            C═O 2,4-Dimethylphenyl                                        411                                                                               Cyclohexylene                                                                            C═O 2,6-Dimethylphenyl                                        412                                                                               Cyclohexylene                                                                            C═O 2,4,6-Trimethylphenyl                                     413                                                                               Cyclohexylene                                                                            C═O 4-tert. Butylphenyl                                       414                                                                               Cyclohexylene                                                                            C═O 1-Naphthyl                                                415                                                                               Cyclohexylene                                                                            C═O 2-Naphthyl                                                416                                                                               Cyclohexylene                                                                            C═O 4-Biphenyl                                                417                                                                               Cyclohexylene                                                                            C═O 2-Fluorophenyl                                            418                                                                               Cyclohexylene                                                                            C═O 4-Fluorophenyl                                            419                                                                               Cyclohexylene                                                                            C═O 2,4-Difluorophenyl                                        420                                                                               Cyclohexylene                                                                            C═O 2-Chlorophenyl                                            421                                                                               Cyclohexylene                                                                            C═O 3-Chlorophenyl                                            422                                                                               Cyclohexylene                                                                            C═O 4-Chlorophenyl    oil 3.1 (s, 2H, --CH.sub.2 -Py)         423                                                                               Cyclohexylene                                                                            C═O 2,4-Dichlorophenyl                                        424                                                                               Cyclohexylene                                                                            C═O 3,4-Dichlorophenyl                                        425                                                                               Cyclohexylene                                                                            C═O 2-Chloro-4-fluorophenyl                                   426                                                                               Cyclohexylene                                                                            C═O 2-Trifluoromethylphenyl                                   427                                                                               Cyclohexylene                                                                            C═O 4-Trifluoromethylphenyl                                   428                                                                               Cyclohexylene                                                                            C═O 4-Methoxyphenyl                                           429                                                                               Cyclohexylene                                                                            C═O 3,4-Dimethoxyphenyl                                       430                                                                               Cyclohexylene                                                                            C═O 4-Tetrafluoroethoxyphenyl                                 431                                                                               Cyclohexylene                                                                            C═O 4-Trifluoromethoxyphenyl                                  432                                                                               Cyclohexylene                                                                            C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       433                                                                               Cyclohexylene                                                                            C═O 4-Phenoxyphenyl                                           434                                                                               Cyclohexylene                                                                            C═O 4-(4'-Chlorophenoxy)phenyl                                435                                                                               Cyclohexylene                                                                            C═O 4-Benzyloxyphenyl                                         436                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O Phenyl                                                    437                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Methylphenyl                                            438                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Methylphenyl                                            439                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2,4-Dimethylphenyl                                        440                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2,6-Dimethylphenyl                                        441                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2,4,6-Trimethylphenyl                                     442                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-tert. Butylphenyl                                       443                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 1-Naphthyl                                                444                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Naphthyl                                                445                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Biphenyl                                                446                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Fluorophenyl                                            447                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Fluorophenyl                                            448                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2,4-Difluorophenyl                                        449                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Chlorophenyl                                            450                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 3-Chlorophenyl                                            451                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Chlorophenyl                                            452                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2,4-Dichlorophenyl                                        453                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 3,4-Dichlorophenyl                                        454                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Chloro-4-fluorophenyl                                   455                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Trifluoromethylphenyl                                   456                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Trifluoromethylphenyl                                   457                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Methoxyphenyl                                           458                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 3,4-Dimethoxyphenyl                                       459                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Tetrafluoroethoxyphenyl                                 460                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Trifluoromethoxyphenyl                                  461                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       462                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Phenoxyphenyl                                           463                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-(4'-Chlorophenoxy)phenyl                                464                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             C═O 4-Benzyloxyphenyl                                         465                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O Phenyl                                                    466                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Methylphenyl                                            467                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Methylphenyl                                            468                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2,4-Dimethylphenyl                                        469                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2,6-Dimethylphenyl                                        470                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2,4,6-Trimethylphenyl                                     471                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-tert. Butylphenyl                                       472                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 1-Naphthyl                                                473                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Naphthyl                                                474                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Biphenyl                                                475                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Fluorophenyl                                            476                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Fluorophenyl                                            477                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2,4-Difluorophenyl                                        478                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Chlorophenyl                                            479                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 3-Chlorophenyl                                            480                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Chlorophenyl                                            481                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2,4-Dichlorophenyl                                        482                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 3,4-Dichlorophenyl                                        483                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Chloro-4-fluorophenyl                                   484                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Trifluoromethylphenyl                                   485                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Trifluoromethylphenyl                                   486                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Methoxyphenyl                                           487                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 3,4-Dimethoxyphenyl                                       488                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Tetrafluoroethoxyphenyl                                 489                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Trifluoromethoxyphenyl                                  490                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 2-Chloro-4-(4'-chlorophenoxy)-phenyl                      491                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Phenoxyphenyl                                           492                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-(4'-Chlorophenoxy)phenyl                                493                                                                               C(CH.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                   C═O 4-Benzyloxyphenyl                                         494                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O Phenyl                                                    495                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Methylphenyl                                            496                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Methylphenyl                                            497                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2,4-Dimethylphenyl                                        498                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2,6-Dimethylphenyl                                        499                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2,4,6-Trimethylphenyl                                     500                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-tert. Butylphenyl                                       501                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 1-Naphthyl                                                502                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Naphthyl                                                503                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Biphenyl                                                504                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Fluorophenyl                                            505                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Fluorophenyl                                            506                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2,4-Difluorophenyl                                        507                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Chlorophenyl                                            508                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 3-Chlorophenyl                                            509                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Chlorophenyl                                            510                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2,4-Dichlorophenyl                                        511                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 3,4-Dichlorophenyl                                        512                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Chloro-4-fluorophenyl                                   513                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Trifluoromethylphenyl                                   514                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Trifluoromethylphenyl                                   515                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Methoxyphenyl                                           516                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 3,4-Dimethoxyphenyl                                       517                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Tetrafluoroethoxyphenyl                                 518                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Trifluoromethoxyphenyl                                  519                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 2-Chloro-4-(4'-chlorophenoxy)phenyl                       520                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Phenoxyphenyl                                           521                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-(4'-Chlorophenoxy)phenyl                                522                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 C═O 4-Benzyloxyphenyl                                         523                                                                               C(CH.sub.3).sub.2                                                                        CHCl    Phenyl            75-80° C.                        524                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Methylphenyl    212-215° C.                      525                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Methylphenyl    108-109° C.                      526                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2,4-Dimethylphenyl                                        527                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2,6-Dimethylphenyl                                        528                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2,4,6-Trimethylphenyl                                                                            215- 218° C.                     529                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-tert. Butylphenyl                                                                              143-147° C.                      530                                                                               C(CH.sub.3).sub.2                                                                        CHCl    1-Naphthyl                                                531                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Naphthyl                                                532                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Biphenyl                                                533                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Fluorophenyl                                            534                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Fluorophenyl                                            535                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2,4-Difluorophenyl                                        536                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Chlorophenyl                                            537                                                                               C(CH.sub.3).sub.2                                                                        CHCl    3-Chlorophenyl                                            538                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Chlorophenyl    155-158° C.                      539                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2,4-Dichlorophenyl                                        540                                                                               C(CH.sub.3).sub.2                                                                        CHCl    3,4-Dichlorophenyl                                        541                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Chloro-4-fluorophenyl                                   542                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Trifluoromethylphenyl                                   543                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Trifluoromethylphenyl                                   544                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Methoxyphenyl                                           545                                                                               C(CH.sub.3).sub.2                                                                        CHCl    3,4-Dimethoxyphenyl                                       546                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Tetrafluoroethoxyphenyl                                 547                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Trifluoromethoxyphenyl                                  548                                                                               C(CH.sub.3).sub.2                                                                        CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       549                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Phenoxyphenyl                                           550                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-(4'-Chlorophenoxy)phenyl                                551                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Benzyloxyphenyl                                         552                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    Phenyl                                                    553                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Methylphenyl                                            554                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Methylphenyl                                            555                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2,4-Dimethylphenyl                                        556                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2,6-Dimethylphenyl                                        557                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2,4,6-Trimethylphenyl                                     558                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-tert. Butylphenyl                                       559                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    1-Naphthyl                                                560                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Naphthyl                                                561                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Biphenyl                                                562                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Fluorophenyl                                            563                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Fluorophenyl                                            564                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2,4-Difluorophenyl                                        565                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Chlorophenyl                                            566                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    3-Chlorophenyl                                            567                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Chlorophenyl                                            568                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2,4-Dichlorophenyl                                        569                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    3,4-Dichlorophenyl                                        570                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Chloro-4-fluorophenyl                                   571                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Trifluoromethylphenyl                                   572                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Trifluoromethylphenyl                                   573                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Methoxyphenyl                                           574                                                                               C(CH.sub.3)(CH.sub. 2 CH.sub.3)                                                          CHCl    3,4-Dimethoxyphenyl                                       575                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Tetrafluoroethoxyphenyl                                 576                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Trifluoromethoxyphenyl                                  577                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       578                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Phenoxyphenyl                                           579                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-(4'-Chlorophenoxy)phenyl                                580                                                                               C(CH.sub.3)(CH.sub.2 CH.sub.3)                                                           CHCl    4-Benzyloxyphenyl                                         581                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    Phenyl            oil 2967, 2939, 1478, 1452, 1423,                                              1027                                    582                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Methylphenyl    153-155° C.                      583                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Methylphenyl                                            584                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2,4-Dimethylphenyl                                        585                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2,6-Dimethylphenyl                                        586                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2,4,6-Trimethylphenyl                                                                            142-146° C.                      587                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-tert. Butylphenyl                                       588                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    1-Naphthyl                                                589                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Naphthyl                                                590                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Biphenyl                                                591                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Fluorophenyl                                            592                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Fluorophenyl                                            593                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2,4-Difluorophenyl                                        594                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Chlorophenyl                                            595                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    3-Chlorophenyl                                            596                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Chlorophenyl                                            597                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2,4-Dichlorophenyl                                        598                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    3,4-Dichlorophenyl                                        599                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Chloro-4-fluorophenyl                                   600                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Trifluoromethylphenyl                                   601                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Trifluoromethylphenyl                                   602                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Methoxyphenyl   87° C.                           603                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    3,4-Dimethoxyphenyl                                       604                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Tetrafluoroethoxyphenyl                                 605                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Trifluoromethoxyphenyl                                  606                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       607                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Phenoxyphenyl                                           608                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-(4'-Chlorophenoxy)phenyl                                609                                                                               C(CH.sub.2 CH.sub.3).sub.2                                                               CHCl    4-Benzyloxyphenyl                                         610                                                                               Cyclopropylene                                                                           CHCl    Phenyl                                                    611                                                                               Cyclopropylene                                                                           CHCl    2-Methylphenyl                                            612                                                                               Cyclopropylene                                                                           CHCl    4-Methylphenyl                                            613                                                                               Cyclopropylene                                                                           CHCl    2,4-Dimethylphenyl                                        614                                                                               Cyclopropylene                                                                           CHCl    2,6-Dimethylphenyl                                        615                                                                               Cyclopropylene                                                                           CHCl    2,4,6-Trimethylphenyl                                     616                                                                               Cyclopropylene                                                                           CHCl    4-tert. Butylphenyl                                       617                                                                               Cyclopropylene                                                                           CHCl    1-Naphthyl                                                618                                                                               Cyclopropylene                                                                           CHCl    2-Naphthyl                                                619                                                                               Cyclopropylene                                                                           CHCl    4-Biphenyl                                                620                                                                               Cyclopropylene                                                                           CHCl    2-Fluorophenyl                                            621                                                                               Cyclopropylene                                                                           CHCl    4-Fluorophenyl                                            622                                                                               Cyclopropylene                                                                           CHCl    2,4-Difluorophenyl                                        623                                                                               Cyclopropylene                                                                           CHCl    2-Chlorophenyl                                            624                                                                               Cyclopropylene                                                                           CHCl    3-Chlorophenyl                                            625                                                                               Cyclopropylene                                                                           CHCl    4-Chlorophenyl                                            626                                                                               Cyclopropylene                                                                           CHCl    2,4-Dichlorophenyl                                        627                                                                               Cyclopropylene                                                                           CHCl    3,4-Dichlorophenyl                                        628                                                                               Cyclopropylene                                                                           CHCl    2-Chloro-4-fluorophenyl                                   629                                                                               Cyclopropylene                                                                           CHCl    2-Trifluoromethylphenyl                                   630                                                                               Cyclopropylene                                                                           CHCl    4-Trifluoromethylphenyl                                   631                                                                               Cyclopropylene                                                                           CHCl    4-Methoxyphenyl                                           632                                                                               Cyclopropylene                                                                           CHCl    3,4-Dimethoxyphenyl                                       633                                                                               Cyclopropylene                                                                           CHCl    4-Tetrafluoroethoxyphenyl                                 634                                                                               Cyclopropylene                                                                           CHCl    4-Trifluoromethoxyphenyl                                  635                                                                               Cyclopropylene                                                                           CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       636                                                                               Cyclopropylene                                                                           CHCl    4-Phenoxyphenyl                                           637                                                                               Cyclopropylene                                                                           CHCl    4-(4'-Chlorophenoxy)phenyl                                638                                                                               Cyclopropylene                                                                           CHCl    4-Benzyloxyphenyl                                         639                                                                               Cyclopentylene                                                                           CHCl    Phenyl                                                    640                                                                               Cyclopentylene                                                                           CHCl    2-Methylphenyl                                            641                                                                               Cyclopentylene                                                                           CHCl    4-Methylphenyl                                            642                                                                               Cyclopentylene                                                                           CHCl    2,4-Dimethylphenyl                                        643                                                                               Cyclopentylene                                                                           CHCl    2,6-Dimethylphenyl                                        644                                                                               Cyclopentylene                                                                           CHCl    2,4,6-Trimethylphenyl                                     645                                                                               Cyclopentylene                                                                           CHCl    4-tert. Butylphenyl                                       646                                                                               Cyclopentylene                                                                           CHCl    1-Naphthyl                                                647                                                                               Cyclopentylene                                                                           CHCl    2-Naphthyl                                                648                                                                               Cyclopentylene                                                                           CHCl    4-Biphenyl                                                649                                                                               Cyclopentylene                                                                           CHCl    2-Fluorophenyl                                            650                                                                               Cyclopentylene                                                                           CHCl    4-Fluorophenyl    oil 2959, 1606, 1510, 1478, 1423,                                              1228                                    651                                                                               Cyclopentylene                                                                           CHCl    2,4-Difluorophenyl                                        652                                                                               Cyclopentylene                                                                           CHCl    2-Chlorophenyl                                            653                                                                               Cyclopentylene                                                                           CHCl    3-Chlorophenyl                                            654                                                                               Cyclopentylene                                                                           CHCl    4-Chlorophenyl    oil 2959, 2873, 1492, 1478, 1423,                                              1408                                    655                                                                               Cyclopentylene                                                                           CHCl    2,4-Dichlorophenyl                                        656                                                                               Cyclopentylene                                                                           CHCl    3,4-Dichlorophenyl                                        657                                                                               Cyclopentylene                                                                           CHCl    2-Chloro-4-fluorophenyl                                   658                                                                               Cyclopentylene                                                                           CHCl    2-Trifluoromethylphenyl                                   659                                                                               Cyclopentylene                                                                           CHCl    4-Trifluoromethylphenyl                                   660                                                                               Cyclopentylene                                                                           CHCl    4-Methoxyphenyl                                           661                                                                               Cyclopentylene                                                                           CHCl    3,4-Dimethoxyphenyl                                       662                                                                               Cyclopentylene                                                                           CHCl    4-Tetrafluoroethoxyphenyl                                 663                                                                               Cyclopentylene                                                                           CHCl    4-Trifluoromethoxyphenyl                                  664                                                                               Cyclopentylene                                                                           CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       665                                                                               Cyclopentylene                                                                           CHCl    4-Phenoxyphenyl                                           666                                                                               Cyclopentylene                                                                           CHCl    4-(4'-Chlorophenoxy)phenyl                                667                                                                               Cyclopentylene                                                                           CHCl    4-Benzyloxyphenyl                                         668                                                                               Cyclohexylene                                                                            CHCl    Phenyl            230° C.                          669                                                                               Cyclohexylene                                                                            CHCl    2-Methylphenyl                                            670                                                                               Cyclohexylene                                                                            CHCl    4-Methylphenyl    213-216° C.                      671                                                                               Cyclohexylene                                                                            CHCl    2,4-Dimethylphenyl                                        672                                                                               Cyclohexylene                                                                            CHCl    2,6-Dimethylphenyl                                        673                                                                               Cyclohexylene                                                                            CHCl    2,4,6-Trimethylphenyl                                     674                                                                               Cyclohexylene                                                                            CHCl    4-tert. Butylphenyl                                       675                                                                               Cyclohexylene                                                                            CHCl    1-Naphthyl                                                676                                                                               Cyclohexylene                                                                            CHCl    2-Naphthyl                                                677                                                                               Cyclohexylene                                                                            CHCl    4-Biphenyl                                                678                                                                               Cyclohexylene                                                                            CHCl    2-Fluorophenyl                                            679                                                                               Cyclohexylene                                                                            CHCl    4-Fluorophenyl    170-173° C.                      680                                                                               Cyclohexylene                                                                            CHCl    2,4-Difluorophenyl                                        681                                                                               Cyclohexylene                                                                            CHCl    2-Chlorophenyl                                            682                                                                               Cyclohexylene                                                                            CHCl    3-Chlorophenyl                                            683                                                                               Cyclohexylene                                                                            CHCl    4-Chlorophenyl    163° C.                          684                                                                               Cyclohexylene                                                                            CHCl    2,4-Dichlorophenyl                                        685                                                                               Cyclohexylene                                                                            CHCl    3,4-Dichlorophenyl                                        686                                                                               Cyclohexylene                                                                            CHCl    2-Chloro-4-fluorophenyl                                   687                                                                               Cyclohexylene                                                                            CHCl    2-Trifluoromethylphenyl                                   688                                                                               Cyclohexylene                                                                            CHCl    4-Trifluoromethylphenyl                                   689                                                                               Cyclohexylene                                                                            CHCl    4-Methoxyphenyl                                           690                                                                               Cyclohexylene                                                                            CHCl    3,4-Dimethoxyphenyl                                       691                                                                               Cyclohexylene                                                                            CHCl    4-Tetrafluoroethoxyphenyl                                 692                                                                               Cyclohexylene                                                                            CHCl    4-Trifluoromethoxyphenyl                                  693                                                                               Cyclohexylene                                                                            CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       694                                                                               Cyclohexylene                                                                            CHCl    4-Phenoxyphenyl                                           695                                                                               Cyclohexylene                                                                            CHCl    4-(4'-Chlorophenoxy)phenyl                                696                                                                               Cyclohexylene                                                                            CHCl    4-Benzyloxyphenyl                                         697                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    Phenyl                                                    698                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Methylphenyl                                            699                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Methylphenyl                                            700                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2,4-Dimethylphenyl                                        701                                                                               C(CH.sub.3)(C.sub. 3 H.sub.7)                                                            CHCl    2,6-Dimethylphenyl                                        702                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2,4,6-Trimethylphenyl                                     703                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-tert. Butylphenyl                                       704                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    1-Naphthyl                                                705                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Naphthyl                                                706                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Biphenyl                                                707                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Fluorophenyl                                            708                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Fluorophenyl                                            709                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2,4-Difluorophenyl                                        710                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Chlorophenyl                                            711                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    3-Chlorophenyl                                            712                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Chlorophenyl                                            713                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2,4-Dichlorophenyl                                        714                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    3,4-Dichlorophenyl                                        715                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Chloro-4-fluorophenyl                                   716                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Trifluoromethylphenyl                                   717                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Trifluoromethylphenyl                                   718                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Methoxyphenyl                                           719                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    3,4-Dimethoxyphenyl                                       720                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Tetrafluoroethoxyphenyl                                 721                                                                               C(CH.sub.3 )(C.sub.3 H.sub.7)                                                            CHCl    4-Trifluoromethoxyphenyl                                  722                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       723                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Phenoxyphenyl                                           724                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-(4'-Chlorophenoxy)phenyl                                725                                                                               C(CH.sub.3)(C.sub.3 H.sub.7)                                                             CHCl    4-Benzyloxyphenyl                                         726                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    Phenyl                                                    727                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Methylphenyl                                            728                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Methylphenyl                                            729                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2,4-Dimethylphenyl                                        730                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2,6-Dimethylphenyl                                        731                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2,4,6-Trimethylphenyl                                     732                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-tert. Butylphenyl                                       733                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    1-Naphthyl                                                734                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Naphthyl                                                735                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Biphenyl                                                736                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Fluorophenyl                                            737                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Fluorophenyl                                            738                                                                               C(C.sub.2 H.sub.5)(n-C.sub. 4 H.sub.9)                                                   CHCl    2,4-Difluorophenyl                                        739                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Chlorophenyl                                            740                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    3-Chlorophenyl                                            741                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Chlorophenyl                                            742                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2,4-Dichlorophenyl                                        743                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    3,4-Dichlorophenyl                                        744                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Chloro-4-fluorophenyl                                   745                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Trifluoromethylphenyl                                   746                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Trifluoromethylphenyl                                   747                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Methoxyphenyl                                           748                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    3,4-Dimethoxyphenyl                                       749                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Tetrafluoroethoxyphenyl                                 750                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Trifluoromethoxyphenyl                                  751                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    2-Chloro-4-(4'-chlorophenoxy)-phenyl                      752                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Phenoxyphenyl                                           753                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-(4'-Chlorophenoxy)phenyl                                754                                                                               C(C.sub.2 H.sub.5)(n-C.sub.4 H.sub.9)                                                    CHCl    4-Benzyloxyphenyl                                         755                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    Phenyl                                                    756                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Methylphenyl                                            757                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Methylphenyl                                            758                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2,4-Dimethylphenyl                                        759                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2,6-Dimethylphenyl                                        760                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2,4,6-Trimethylphenyl                                     761                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-tert. Butylphenyl                                       762                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    1-Naphthyl                                                763                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Naphthyl                                                764                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Biphenyl                                                765                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Fluorophenyl                                            766                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Fluorophenyl                                            767                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2,4-Difluorophenyl                                        768                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Chlorophenyl                                            769                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    3-Chlorophenyl                                            770                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Chlorophenyl                                            771                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2,4-Dichlorophenyl                                        772                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    3,4-Dichlorophenyl                                        773                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Chloro-4-fluorophenyl                                   774                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Trifluoromethylphenyl                                   775                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Trifluoromethylphenyl                                   776                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Methoxyphenyl                                           777                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    3,4-Dimethoxyphenyl                                       778                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Tetrafluoroethoxyphenyl                                 779                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Trifluoromethoxyphenyl                                  780                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    2-Chloro-4-(4'-chlorophenoxy)phenyl                       781                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Phenoxyphenyl                                           782                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-(4'-Chlorophenoxy)phenyl                                783                                                                               CH(tert.C.sub.4 H.sub.9)                                                                 CHCl    4-Benzyloxyphenyl                                         784                                                                               C(CH.sub.3).sub.2                                                                        CHOH    3-Methylphenyl    86-88° C.                        785                                                                               C(CH.sub.3).sub.2                                                                        CHOH    2-Methoxyphenyl   128-130° C.                      786                                                                               C(CH.sub.3).sub.2                                                                        CHOH    3-Fluorophenyl    3200, 2965, 1589, 1480, 1046            787                                                                               C(CH.sub.3).sub.2                                                                        CHOH    4-Isopropylphenyl 97-98° C.                        788                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHOH    3-Methylphenyl    3200, 2963, 1424, 1030, 716             789                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHOH    3-Trifluoromethylphenyl                                                                          117-119° C.                      790                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHOH    2-Methoxyphenyl   3200, 2962, 1488, 1238, 1030, 755       791                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHOH    3-Fluorophenyl    3200, 2966, 1589, 1480, 1258            792                                                                               Cyclopentylene                                                                           CHOH    3-Trifluoromethylphenyl                                                                          3200, 2956, 1329, 1163, 708             793                                                                               Cyclopentylene                                                                           CHOH    3-Methylphenyl    3236, 2952, 1425, 1030, 717             794                                                                               Cyclopentylene                                                                           CHOH    2-Methoxyphenyl   94-98° C.                        795                                                                               Cyclopentylene                                                                           CHOH    4-tert.-Butylphenyl                                                                              106-108° C.                      796                                                                               Cyclopentylene                                                                           CHOH    3-Fluorophenyl    3200, 2954, 1588, 1030, 717             797                                                                               Cyclopentylene                                                                           CHOH    4-Isopropylphenyl 3227, 2957, 1424, 1030, 717             798                                                                               Cyclohexylene                                                                            CHOH    3-Methylphenyl    137-139° C.                      799                                                                               Cyclohexylene                                                                            CHOH    4-Isopropylphenyl 98-100° C.                       800                                                                               Cyclohexylene                                                                            CHOH    3-Trifluoromethylphenyl                                                                          3180, 2931, 1510, 1244, 1038, 713       801                                                                               Cyclohexylene                                                                            CHOH    2-Methoxyphenyl   141-142° C.                      802                                                                               Cyclohexylene                                                                            CHOH    3-Fluorophenyl    146-148° C.                      803                                                                               C(CH.sub.3).sub.2                                                                        CHCl    3-Methylphenyl    144-146° C.                      804                                                                               C(CH.sub.3).sub.2                                                                        CHCl    3-Fluorophenyl    165-167° C.                      805                                                                               C(CH.sub.3).sub.2                                                                        CHCl    4-Isopropylphenyl 104-108° C.                      806                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHCl    3-Trifluoromethylphenyl                                                                          66-69° C.                        807                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHCl    3-Fluorophenyl    205-207° C.                      808                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHCl    3-Methylphenyl    107-110° C.                      809                                                                               C(C.sub.2 H.sub.5).sub.2                                                                 CHCl    2-Methoxyphenyl   83° C.                           810                                                                               Cyclopentylene                                                                           CHCl    2-Methoxyphenyl   142-143° C.                      811                                                                               C(CH.sub.3).sub.2                                                                        C═NOCH.sub.3                                                                       4-Chlorophenyl    47-49° C.                        812                                                                               C(CH.sub.3).sub.2                                                                        C═NOCH.sub.3                                                                       4-Methylphenyl    159-161° C.                      813                                                                               C(CH.sub.3).sub.2                                                                        C═NOCH.sub.3                                                                       4-Fluorophenyl    2970, 1507, 1423, 1224, 1067            814                                                                               Cyclopentylene                                                                           C═NOCH.sub.3                                                                       4-Fluorophenyl    138-140° C.                      __________________________________________________________________________

In general terms, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the class consisting of the Ascomycetes and Basidiomycetes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, cots, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphgaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in applies,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton and lawns,

Ustilago species in ceraisland suga cane,

Venturia inaequalis (scab) in applies,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cersospora arachidicola in ground nuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi, or the plants, seed or materials to be protected against fungus attack, or the soil, are treated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as ligninsulfite waste liquors and methylcellulose.

The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt. % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials, e.g., against Paecilomyces variotii. When the active ingredients are used for treating seed, generally amounts of from 0.001 to 50, and preferably from 0.01 to 10, g per kg of seed are required.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. A solution of 90 parts by weight of compound no. 1 and 10 parts by weight of N-methyl-α-pyrrolidone, which is suitable for application in the form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 3, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in water, an aqueous dispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 12, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By finely dispersing the mixture of water, an aqueous dispersion is obtained.

IV. An aqueous dispersion of 20 parts by weight of compound no. 16, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.

V. A hammer-milled mixture of 80 parts by weight of compound no. 30, 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 pats by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the mixture in water, a spray liquor is obtained.

VI. An intimate mixture of 3 parts by weight of compound no. 32 and 97 parts by weight of particulate kaolin. The dust contains 3 wt. % of the active ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 41, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica gel. This formulation of the active ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no. 45, 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 61, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

In these application forms, the agents according to the invention may also be present together with other active ingredients, for example herbicides, insecticides, growth regulators, and fungicides, and may furthermore be mixed and applied together with fertilizers. Admixture with other fungicides frequently results in a greater fungicidal action spectrum.

USE EXAMPLES

The active ingredient used for comparison purposes was 1-phenyl-3-(3-pyridinyl)-propan-1-one (A) disclosed in J. Org. Chem., Vol. 43 (1978), p. 3396.

Use Example 1 Action on Alternaria solani

Potted tomato plants of the "Groβe Fleischtomat" variety grown in the greenhouse were sprayed to runoff at the 4-leaf stage with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the leaves were inoculated with an aqueous spore suspension of the fungus Alternaria solani. These plants were then placed in a water vapor-saturated chamber at from 22 to 24° C. After 4 days, the disease had spread on the untreated but inoculated plants to such a great extent that the fungicidal action of the compounds was able to be assessed.

The results show that active ingredients 1, 3, 12, 16, 30, 32, 41, 45, 61, 74, 117, 119, 128, 132, 133, 161, 175, 177, 186, 204, 206, 215 and 219, applied as 0.05 wt. % spray liquors, have a better fungicidal action (95%) than prior art comparative active ingredient A (10%).

Use Example 2 Action on Botrytis cinerea in paprika

Paprika seedlings of the "Neusideler Ideal Elite" variety were sprayed, after 4 to 5 leaves were well developed, to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient ad 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprinkled with a conidial suspension of the fungus Botrytis cinerea, and placed at 22 to 24°° C. in a chamber of high humidity. After 5 days, the disease had spread to such a great extent on the untreated plants that the necroses covered the major portion of the leaves.

The results show that active ingredients 3, 16, 32, 45, 59, 61, 70, 132, 133, 177, 190, 206, 215 and 219, applied as 0.05 wt. % spray liquors, have a better fungicidal action (95%) than prior art comparative agent A (30%).

Use Example 3 Action on Pyrenophora teres

Leaves of pot-grown barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up in high-humidity climatic cabinet at 18° C. The plants were then cultivated for a further 5 days at 20 to 22° C. and a relative humidity of 70%. The extent of leaf attack was then assessed.

The results show that active ingredients 1, 3, 12, 16, 32, 45, 61, 70, 74, 117, 119, 128, 132, 133, 157, 161, 177, 186, 204, 206, 215, 219, 650 and 683, applied as 0.05 wt % spray liquors, have a better fungicidal action (95%) than prior art comparative agent A (30%). 

We claim:
 1. A member selected from the group consisting of a β-picoline derivative of the formula ##STR10## where A is CR¹ R²,R¹ and R² independently of one another are each hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl or R¹ and R² together form a methylene chain having from 2 to 6 methylene groups, B is one of the groups of CH₂, CHOR³, CHR⁴, C═O or C═N--O--R⁵, R³ is hydrogen, C₁ -Ch₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆ -alkenyl, C₂ -C₆ -acyl, phenyl, benzyl or benzoyl, where the phenyl ring may be unsubstituted or substituted by from one to three substituents selected from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ C₄ -haloalkoxy, halogen, cyano and nitro, R⁴ is fluorine, chlorine, bromine or iodine, R⁵ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₇ -cycloalkyl, C₃ -C₆ -alkenyl or aralkyl where the alkyl radical is of 1 to 4 carbon atoms and the aryl radical may be unsubstituted or substituted by from one to three substituents selected from the groups consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, cycano and nitro, and Ar is a phenyl or naphthyl radical which is unsubstituted or monosubstituted to trisubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C.sub. 4 -haloalkoxy, phenyl, phenoxy, halophenyl, halophenoxy or benzyloxy, its N-oxides and plant-tolerated acid addition salts, except for the compound in which A is CH₂, B is C═O and Ar is phenyl.
 2. A fungicidal composition containing an inert carrier and a fungicidal amount of a β-picoline derivative of the formula ##STR11## where A is CR¹ R² R¹ and R² independently of one another are each hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl or R¹ and R² together form a methylene chain having from 2 to 6 methylene groups, B is one of the groups of C₂ CHOR³, CHR⁴, C═O or C═N--O--R⁵ R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆ -alkenyl, C₂ -C₆ -acyl, phenyl, benzyl or benzoyl, where the phenyl ring may be unsubstituted or substituted by from one to three substituents selected from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, halogen, cyano and nitro, R⁴ is fluorine, chlorine, bromine or iodine, R⁵ is hydrogen, C₁ -C₆ -alkyl, Chd 1-C₆ -haloalkyl, C₃ -C₇ -cycloalkyl, C₃ -C₆ -alkenyl or aralkyl where the alkyl radical is of 1 to 4 carbon atoms and the aryl radical may be unsubstituted or substituted by from one to three substituents selected from the groups consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C.sub. 1 -C₄ -haloalkyl, halogen, cyano and nitro, and Ar is a phenyl or naphthyl radical which is unsubstituted or monosubstituted to trisubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, phenyl, phenoxy, halophenyl, halophenoxy or benzyloxy, or its N-oxide or plant-tolerated acid addition salt, except for the compound in which A is CH₂, B is C═O and Ar is phenyl.
 3. A method for controlling fungi, wherein the fungi or the materials, plants, soils or seeds threatened by fungal attack are treated with a fungicidal amount of a β-picoline derivative of the formula I ##STR12## where A is CR¹ R².R¹ and R² independently of one another are each hydrogen, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl or C₂ -C₆ -alkynyl or R¹ and R² together form a methylene chain having from 2 to 6 methylene groups, B is one of the groups CH₂, CHOR³, CHR⁴, C═O or C═N--O--R⁵, R³ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₈ -cycloalkyl, C₃ -C₆ -alkenyl, C₂ -C₆ -acyl, phenyl, benzyl or benzoyl, where the phenyl ring maybe unsubstituted or substituted by from one to three substituents selected from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, halogen, cyano and nitro, R⁴ is fluorine, chlorine, bromine or iodine, R⁵ is hydrogen, C₁ -C₆ -alkyl, C₁ ∝C₆ -haloalkyl, C₃ -C₇ -cycloalkyl, C₃ -C₆ -alkenyl or aralkyl where the alkyl radical is of 1 to 4 carbon atoms and the aryl radical may be unsubstituted or substituted by from one to three substituents selected from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, cyano and nitro, and Ar is a phenyl or naphthyl radical which is unsubstituted or substituted by from one to three substituents selected from the group consisting of C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, cyano and nitro, and Ar is a phenyl or naphthyl radical which is unsubstituted or monosubstituted to trisubstituted by halogen, C₁ -C₆ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₄ -haloalkoxy, phenyl, phenoxy, halophenyl, halophenoxy or benzyloxy, or its N-oxide or plant-tolerated acid addition salt.
 4. A compound as claimed in claim 1, wherein A is C(C₂ H₅)₂, B is C═O and Ar is 4-fluorophenyl.
 5. A compound as claimed in claim 1, wherein A is C(C₂ H₅)₂, B is CHCl and Ar is 4-fluorophenyl.
 6. A compound as claimed in claim 1, wherein B is C═O.
 7. A compound as claimed in claim 1, wherein B is CHOH.
 8. A compound as claimed in claim 1, wherein B is CHCl.
 9. A compound as claimed in claim 1, wherein B is C═NOR⁵.
 10. A compound as claimed in claim 1, wherein A is cyclopentylene, B is CHOH, and Ar is 4-iopropylphenyl. 